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Breathtaking Hiking Trails to Explore on Long Island and Upstate New York

Written by Contour Mortgage | Jun 7, 2025 8:45:52 PM

Whether you're a seasoned hiker or just looking for a scenic walk, New York offers some of the most beautiful trails on the East Coast. From coastal views in Montauk to rugged mountain climbs upstate, thereโ€™s a hike for every pace and personality. Here are 8 of the best hiking trails across Long Island and Upstate New York to add to your adventure list.


 

1. Cold Spring Harbor Trail

๐Ÿ“ Cold Spring Harbor, NY
Park Website
This hilly 1.8-mile loop is a local favorite on Long Island's North Shore. The trail offers shaded forest paths, scenic views of the harbor, and a great workout thanks to its elevation changes. It's beautiful in every season, especially fall.

 

 

 

2.  Montauk Point Loop  

 ๐Ÿ“ Montauk, NY
AllTrails Listing
Take in dramatic Atlantic Ocean views along this 4-mile coastal loop at the easternmost tip of Long Island. With rocky beaches, lighthouse views, and salty breezes, this hike is as photogenic as it is refreshing. 

 

 

3. Massapequa Lake Trail

๐Ÿ“ Massapequa, NY
AllTrails Listing | Park Info
Perfect for beginners or a peaceful walk, this flat, tree-lined path winds past lakes, streams, and wooden bridges. It's a nature escape right in the heart of Nassau County.

 

 

4.  Norman J. Levy Park & Preserve Walking Trails 

๐Ÿ“ Merrick, NY
Town of Hempstead Info | TripAdvisor Reviews
This eco-friendly preserve features crushed gravel trails, bay views, and even a herd of Nigerian dwarf goats helping maintain the landscape. Itโ€™s a great place for walking, wildlife spotting, and catching sunset views over the water.

 

 

5. Bear Mountain Loop Trail  

๐Ÿ“ Bear Mountain, NY
AllTrails Listing
One of the most iconic hikes in the Hudson Valley, this 4.3-mile loop features stone stairs, forest trails, and sweeping views of the Hudson River from Perkins Memorial Tower. Itโ€™s steep in sections but worth every step.

 

 

6.  Breakneck Ridge   

๐Ÿ“ Hudson Highlands State Park Preserve
AllTrails Listing
One of the most iconic hikes in the Hudson Valley, this 4.3-mile loop features stone stairs, forest trails, and sweeping views of the Hudson River from Perkins Memorial Tower. Itโ€™s steep in sections but worth every step.

7.  Glen Creek Gorge Trail  

๐Ÿ“ Watkins Glen State Park

 AllTrails Listing
Step into a fairytale on this 2.4-mile trail through Watkins Glenโ€™s gorge. With 19 waterfalls, stone bridges, and winding staircases, this is one of the most awe-inspiring and accessible hikes in New York State. 

8.  Lake Minnewaska Carriage Road Loop  

 ๐Ÿ“ Minnewaska State Park Preserve
AllTrails Listing
A gentle but scenic loop, this 4.2-mile trail circles the crystal-clear Lake Minnewaska. Surrounded by cliffs and forests, itโ€™s perfect for a serene hike, bike ride, or picnic stop. 

 Final Thoughts 

 From Long Islandโ€™s peaceful preserves to the dramatic heights of the Hudson Valley, New York is filled with trails that cater to every explorer. Whether you're hiking for views, fresh air, or a little weekend Zen, these trails are your invitation to get outside and explore more.